When Claude is unexpectedly asked out for dinner with Will, she quickly cancels her double-date plan with Ramona. But when the ""date"" turns out to be less of one than she anticipated, Claude finds solace in the company of Lydia -- who assumes that Claude slept with him. Meanwhile, Owen tries to assert authority over Kipp and the two feud over an expensive pen.

Claude sees herself struggling with her moral values when she is forced to lie for Will. She feels bad about covering up one of Will's escapades and lying to Ramona and his wife about it, but it's all good after Claude talks to Ramona. Meanwhile, the employees attend a companywide meeting where they have to pick a "floor buddy", someone from another floor for them to bond with. Lydia is at first annoyed by Owen but later misses him after she realizes he treated her like no one else did. And Ramona and Kipp pretend to dislike each other after having a great time in the Hamptons.

Feeling jealous over Claude being showered by gifts for being Will Butler's assistant, Kipp and Lydia try to break Claude, Ramona and Owen's friendship. Kipp tells Claude that Will doesn't like her having her 4th floor friends around his office, which Claude believes. She politely asks them to stay on their floor, which they take offensively. Now Claude feels bad for sending her friends away, and tries to work her way back into their friendship circle. Meanwhile, Lydia struggles with her (lack of) good sense after she feels guilty for switching Ramona's original Prada hangbag for a cheap imitation. She was trying o save the purse from being ""killed"" by Ramona's exquisite fashion taste and personal alterations on the wonderful Italian leather.

Ramona tells Claude she has to use her vacation days in the next few days or else she'll lose them. Claude refuses to leave Will even for a week, and Ramona (trying to be a good friend and give Claude a break from her overbearing work) sends a memo to Will about Claude's vacation. Forced to take a break, Claude pretends to go to Niagra Falls and sneaks around the office when she meets her temporary replacement – who she thinks might take her job. Ultimately, Will reassures her she doesn't have to worry about her job; he wouldn't trade her for the world. As for Kipp's dream job of becoming an associate producer, well, that will have to wait a little longer. Torturing Claude with lies about Luke's resume might have given Luke a promotion he never expected in such short notice.

Tired of living in constant competition with Lydia over Will's attention, Claude decides to attend Ramona's ""strippercize"" class to develop her ""uh-uh"". Claude quickly gains the self-confidence that she's been lacking, so she and Ramona go out for drinks, where Claude finds herself competing for men -- against Lydia. Meanwhile, Kipp asks for Owen to help him take a good picture for his id card, and Owen obliges... but Kipp soon discovers that Owen is too much of a perfectionist.

Claude accidentally starts a feud with Roz, the company's president's secretary, but being the good hearted girl that she is she wastes no time on trying her best to make up with Roz. Roz sees in Claude a younger version of herself and tells Claude that will be her in 30 years, and Claude freaks out about it after realizing that indeed she has no personal life outside the workplace. She joins a pottery class and tries to make a gravy boat that ends up looking like a squirrel. Lastly, she tells Will she loves working for him, but doesn't want to be stuck as a secretary all her life. Will assures her she's very talented and can be anything she wants. Meanwhile, Kipp buys a 1500 dollar Armani suit and Owen thinks he bought it from him for a hundred bucks after he lent it to Kipp. When Owen doesn't hold the elevator door for Roz, she prepares her revenge. When Kipp shows up for an interview with the company president, Roz retaliates on him, thinking he was the one to leave her waiting in t

Claude's parents are visiting her at the office, and can't wait to meet famous anchorman Will Butler. They invite him to join them for dinner and Will says ""that would be great"", leading the Caseys to think he will show up, when in fact he won't since """"that would be great"" means ""ain't gonna happen"". Claude doesn't know how to break the news to her parents, and takes the blame for it. They are disappointed at Will, and embarrass Claude by giving him a lecture when he decides to surprise Claude and show up unexpectedly. Meanwhile, Kipp is idolized by a college student and falls for her, only to get his heart broken after she gets a job as associate producer at CNN and he is left alone with his lies.

Claude scores a date with Charlie from travel after accidentally throwing her hair on his face. They have a wonderful time together, and the next morning Claude is ecstatic about it. Will introduces her his godson Oliver, and asks Claude to show him around town. He asks her out on a date, and ends up accepting to go out with him after Will pressures her to. Claude tries to jiggle dating two men, but her scheme soon falls apart when Will comments on her date with Oliver in front of Charlie, who leaves heartbroken. Claude feels bad gets advice from Ramona and Lydia on how to dump Oliver and get back with Charlie. Meanwhile, Kipp starts sucking up to Mr. Turnbach's son hoping for a chance of a promotion.

It's time for the Christmas party, and Claude keeps hanging around Will, making sure he's got everything just the way he wants. When he tells her to loosen up a bit and act casual because she's not on the clock, Claude gets a little too personal and talks about Will's personal life. She spends the rest of the party worrying about the impression she gave and tries to make up for it, but only make things worse when she accidentally tells Will she had a crush on him. Meanwhile, Kipp keeps trying to find some big-shot producer who will promote him, and after a number of unsuccessful attempts he announces on the mic he's quitting. Ramona is a big success with her enormous cleavage and Owen and Lydia end up making out after both have a lousy time at the party. The next morning, Kipp tells Claude nothing that happens on the Christmas party counts, and she thinks twice about the cute guy she met on the bar.

Kipp broke Claude's penguin toy, but instead of planning a meaningful revenge against him, Claude decides to help him make a demo tape on which he can show his news anchor abilities and she can show her producer skills. Of course, Kipp's attitude on the newsset it completely corky, which ends up as a very funny – and very humiliating – demo tape. But Claude is too good hearted to let Kipp go through that kind of embarrassment in front of everyone and decides to destroy the tape (and Kipp's trust on her). Meanwhile, Lydia tries to prove that Will hasn't forgotten about their night together and ends up realizing she is the one who forgot about it.

Ramona and Owen wonder why Charlie and Claude stopped seeing each other, while they have been secretly dating, trying to keep a low profile on a inner-office relationship. But that is no easy task since Ramona and Owen seem to be all over the place. Claude talks Charlie into telling their friends, which he agrees on since she trusts them so much. The next day everyone in the building knows about it, which makes them very uncomfortable. The solution? Go back to how things were. They break up in public and go back to their little secret affair. Meanwhile, Lydia asks big shot Norma Craft to be her mentor, but ends up being the listener to all her personal problems. Seeing that her scheme is taking her nowhere she hoped it would, she decides to pull the plug on it – just in time, as Norma was planning to set cat's poop on fire on Alan Turnbach's table!

Will leaves his apartment to be taken care by Claude while he's gone, and tells her she can bring whoever she wants to it. She quickly organizes a small party just for her closest friends, which does not include Kipp, who stole her idea for a story. Lydia gets obsessed in finding a crystal gazelle she gave to Will and after she does she spends the whole evening trying to rescue it from the fish tank. Kipp drops by unannounced and discovers by accident that Will has his mom's phone number on his speed dial. Turns out his mother and Will have been sleeping together for a good time now, which causes a lot of awkwardness on both parties, and it's up to Claude to fix things.

Will's got a new girlfriend, Dani, who insists on having Claude run errands for her. Ramona and Owen convince Claude to put her feet down and stop being a pushover for Dani. When she finally confronts Will's new girlfriend, she imposes him to choose between her and Claude. Although happy to see Dani out of her life, Claude has to put aside the pride and talk her into getting back together with Will, who's been miserable without her. Meanwhile, Lydia and Kipp start sucking up to Ramona and Owen when they find out they have access to the VIP area at an important party.

It's Valentine's Day and Lydia is feeling jealous of Claude over a dozen roses she got from Charlie, who's on a road trip with his father. The next morning, two dozen roses mysteriously appear on Lydia's desk, and she wonders who is her secret admirer. Claude finds out it's Kipp, but decides to keep it down because no one would believe that. Meanwhile, Claude has the most embarrassing moment of her life when Will overhears her talking dirty with Kipp on the phone; and Owen is seduced by a gorgeous girl who only wants his sperm to make a baby, leaving Claude and Ramona the mission of opening his eyes not to let a child grow without a father.

After breaking up with Charlie, Claude is feeling low. Will's fiance insists Claude accompany her to a bridal salon, which only serves to upset Claude further. They run into Trista Rehn (star of ABC's reality show, The Bachelorette), who got engaged on the show and is trying on wedding gowns. Claude locks herself in a dressing room to cry, wiping her nose on a wedding gown, and Trista trys to comfort her through the door. Claude's friends rally round, even Lidia, and try to cheer Claude with an impromptu slumber party and girl talk.

In celebration of two years in NY, Claude decides to throw a party at her place. But when Will says he'll go (a direct result from his publicist's attempt to popularize his image), she changes her party from casual to fancy. The only thing she wasn't counting on was Will showing up in casual clothes and turning her party into exactly what she wanted to avoid. In the end Ramona questions Claude about the reasons of her sadness and shows her that even though her party might not be the fanciest people sure are having fun.

Will's contract is up for renewal just as the head of the network arrives, flaunting a new anchor. Fearing that Will's job is in jeopardy and they'll be replaced, the staff bands together to pull of ""The Gum Caper"" to ensure Will a new contract.

Learning that Owen has ""sired"" a child, Claude tries to arrange a get-together between Owen and the dad he's never known. When ""braces guy"" gets a promotion, Kipp decides that he needs a gimmick to get noticed -- so he becomes ""bicycle guy."" A bad photo in the paper has Will feeling self-conscious about aging, so he recruits Lydia to make him over.

Claude's brother shows up for a visit and Lydia is quickly interested in him. While the thought of the two dating disturbs Claude at first, she comes to terms with it once she sees how happy (and nicer) is makes Lydia. But she accidentally tells her brother that Lydia is crazy about him, and he decides to dump her. Lydia is devastated and it's up to Claude to clear things out. Meanwhile, Owen states on the inner-office magazine that he beats Will on chess all the time and Will comes down to challenge him.

Claude hawks tickets to Will's benefit dinner for a squirrel clinic, Owen gets in trouble with a bookie, and Kipp & Lydia scheme to get free merchandise.

Claude's new sway jacket is ruined because someone stole her umbrella, forcing her to go out in the rain. When she returns to the building, however, she runs into the guy who stole it and confronts him, only to find out later that he's Ted Elliot, the new executive producer. With her job on jeopardy, Claude has a change of attitude, but Ted is such a jerk to everyone that she stands up for her morals. Impressed, Ted offers her a job as his assistant, leaving Claude with a dilemma: does she continue to work for her beloved Will Butler or does she dump him for a job with a much more promising future ahead of her? To be Continued...